Synthesis of Chiral Vicinal Amino Alcohol Derivatives via Lewis Acid-Catalyzed Asymmetric Ring Opening of Aziridines with Alcohols and Carboxylic Acids
Synthesis of Chiral Vicinal Amino Alcohol Derivatives via Lewis Acid-Catalyzed Asymmetric Ring Opening of Aziridines with Alcohols and Carboxylic Acids
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DOI：
10.1002/adsc.202301429
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发表时间：
2024-02-21
影响因子：
5.4
通讯作者：
Chai，Zhuo
中科院分区：
文献类型：
--
作者：
Ma，Chen-Xue;Hu，Qi;Chai，Zhuo
在Cu（I）或Ag（I）盐与手性双膦配体的催化下，实现了外消旋2-苯乙烯基氮杂环丙烷的动力学拆分或动态动力学不对称转化（DyKAT）以及内消旋氮杂环丙烷与醇的去对称化反应的对映选择性亲核开环.该反应以47%-98%的产率和50%-98%ee提供了一系列手性邻位氨基醚衍生物。该反应可以扩展到脂肪族羧酸作为亲核试剂。在抗心律失常剂维那卡兰的非对映异构体的四步正式合成中证明了合成效用。
Under the catalysis of a Cu(I) or Ag(I) salt with a chiral diphosphine ligand, the enantioselective nucleophilic ring opening of racemic 2‐styrenylaziridines via kinetic resolution or dynamic kinetic asymmetric transformation (DyKAT) and of meso aziridines via desymmetrization with alcohols was realized. The reaction provided a range of chiral vicinal amino ether derivatives in 47%‐98% yields and with 50%–98% ee. The reaction could be extended to aliphatic carboxylic acids as nucleophiles. The synthetic utility was demonstrated in a four‐step formal synthesis of a diastereomer of the antirythmetic agent vernakalant.